Caroline Cummings is a serial entrepreneur who has been the CEO and co-founder of two technology companies in Eugene. She’s raised close to $1 million in angel capital for her ventures and has coached other entrepreneurs on how to raise capital. Caroline is also the Venture Catalyst for Oregon RAIN (Regional Accelerator & Innovation Network), where she connects entrepreneurs to the resources they need to start and scale their ventures. Additionally, she’s the venture associate for the new seed fund Willamette Valley Capital.
Mentorship Matters
How to find and get what you need from mentors
Article by CAROLINE CUMMINGS, VENTURE CATALYST FOR OREGON RAIN | Photo by PALO ALTO SOFTWARE
I like to say, “Everyone should have a mentor and be mentored.” It’s because mentorship works. I’ve seen it help many people achieve success, personally and professionally.
I attribute much of my own success to having mentors. These are people I call on to help me think through challenging situations. And over the years, I’ve had many mentors with a variety of expertise, including finance, leadership, sales, marketing and investing. Between literature and film, business and politics, we are surrounded by great examples of mentor relationships. And yet, most people don’t know how to find and get what they need from a mentor.
When we decide we need a mentor, our first impulse is to ask the most successful person we know. But that isn’t the best path. Before you make any calls, spend some time thinking about exactly what you want to achieve. Then, ask people in your network if they know someone with that expertise.
Once you have a lead, begin by asking them out for coffee and an informational interview; tell them you’d like to know what steps they took in their career, because you’re interested in doing something similar. After this initial (less than 30 minutes) meeting, if you feel there’s potential for a strong, mutual rapport, then you can ask them to be your mentor.
You might say, “I’d like to spend the next three months becoming better at sales, and I would be honored if you would help me. Would you be willing to meet with me for 30 minutes every other week?”
I attribute much of my own success to having mentors. These are people I call on to help me think through challenging situations. And over the years, I’ve had many mentors with a variety of expertise, including finance, leadership, sales, marketing and investing. Between literature and film, business and politics, we are surrounded by great examples of mentor relationships. And yet, most people don’t know how to find and get what they need from a mentor.
When we decide we need a mentor, our first impulse is to ask the most successful person we know. But that isn’t the best path. Before you make any calls, spend some time thinking about exactly what you want to achieve. Then, ask people in your network if they know someone with that expertise.
Once you have a lead, begin by asking them out for coffee and an informational interview; tell them you’d like to know what steps they took in their career, because you’re interested in doing something similar. After this initial (less than 30 minutes) meeting, if you feel there’s potential for a strong, mutual rapport, then you can ask them to be your mentor.
You might say, “I’d like to spend the next three months becoming better at sales, and I would be honored if you would help me. Would you be willing to meet with me for 30 minutes every other week?”
The key to a successful mentor relationship is establishing timelines, guidelines and following through on your commitments. For example, I will assign tasks for my mentees to complete by our next meeting, and if they don’t do those tasks, or stop communicating with me, I have to have a conversation with them about how the relationship is not working.
It’s also important to establish boundaries and be transparent about your goals. Since I’ve co-founded and led startups, and now help run a seed capital fund, entrepreneurs regularly ask me to mentor them or help find them a mentor. The more prepared they are and understand what areas they want to improve, the easier it is for me to help match them with the right mentor. When it’s time to conclude the relationship, be sure to send your mentor a thank-you note, preferably handwritten. Thank them for their time and point out, specifically, how they helped you advance your goals.
This would also be an appropriate time to ask them for connections to other potential mentors, because there are so many ways that you can continue to develop personally and professionally.
Locally, the Eugene Young Professionals program and Business After Hours events—both hosted by the Eugene Area Chamber of Commerce—are great places to connect with potential mentors. Also, the RAIN Eugene Accelerator has a large database of mentors for
It’s also important to establish boundaries and be transparent about your goals. Since I’ve co-founded and led startups, and now help run a seed capital fund, entrepreneurs regularly ask me to mentor them or help find them a mentor. The more prepared they are and understand what areas they want to improve, the easier it is for me to help match them with the right mentor. When it’s time to conclude the relationship, be sure to send your mentor a thank-you note, preferably handwritten. Thank them for their time and point out, specifically, how they helped you advance your goals.
This would also be an appropriate time to ask them for connections to other potential mentors, because there are so many ways that you can continue to develop personally and professionally.
Locally, the Eugene Young Professionals program and Business After Hours events—both hosted by the Eugene Area Chamber of Commerce—are great places to connect with potential mentors. Also, the RAIN Eugene Accelerator has a large database of mentors for
Chamber Connection
Sign-up for the next meeting of the Eugene Young Professionals or Business After Hours and connect with local business leaders and mentors. Visit the Chamber calendar for monthly events at EugeneChamber.com.
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